A Review on the Preparation of 1,3,4-Oxadiazoles From the Dehydration of Hydrazines and Study of Their Biological Roles

Nayak, Soukhyarani Gopal; Poojary, Boja

doi:10.1007/s42250-019-00084-9

“…Traditional syntheses of α‐amino 1,3,4‐oxadiazoles are largely based on indirect condensation approaches where the oxadiazole unit is constructed through dehydration of a 1,2‐diacylhydrazine. [ 2k , 4 ] The need for multistep synthesis, and harsh dehydration conditions typically dictates that the oxadiazole be introduced at an early stage in the synthetic sequence, and thus a direct and late‐stage introduction of this motif would be both desirable and enabling. [5]…”

mentioning

confidence: 99%

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

Matheau‐Raven

¹

,

Dixon

²

2021

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An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska's complex (IrCl(CO)(PPh 3) 2 ) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates. File list (2) download file view on ChemRxiv VaskaOxadiazoles -ChemRxiv.pdf (1.02 MiB) download file view on ChemRxiv VaskaOxadiazolesSI.pdf (4.98 MiB)

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“…[ 71 , 72 , 73 , 74 ]. Hence, oxadiazole is considered a significant heterocyclic core and becomes a major scaffold for the development of new drug candidates because of its potential to be involved in the binding interactions with different targets or receptors with suitable metabolic profile [ 75 , 76 , 77 , 78 ].…”

Section: Future Developmentmentioning

confidence: 99%

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

Banik

¹

,

Sahoo

²

,

Kumar

³

et al. 2021

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Green synthetic protocol refers to the development of processes for the sustainable production of chemicals and materials. For the synthesis of various biologically active compounds, energy-efficient and environmentally benign processes are applied, such as microwave irradiation technology, ultrasound-mediated synthesis, photo-catalysis (ultraviolet, visible and infrared irradiation), molecular sieving, grinding and milling techniques, etc. Thesemethods are considered sustainable technology and become valuable green protocol to synthesize new drug molecules as theyprovidenumerous benefits over conventional synthetic methods.Based on this concept, oxadiazole derivatives are synthesized under microwave irradiation technique to reduce the formation of byproduct so that the product yield can be increased quantitatively in less reaction time. Hence, the synthesis of drug molecules under microwave irradiation follows a green chemistry approach that employs a set of principles to minimize or remove the utilization and production of hazardous toxic materials during the design, manufacture and application of chemical substances.This approach plays a major role in controlling environmental pollution by utilizing safer solvents, catalysts, suitable reaction conditions and thereby increases the atom economy and energy efficiency. Oxadiazole is a five-membered heterocyclic compound that possesses one oxygen and two nitrogen atoms in the ring system.Oxadiazole moiety is drawing considerable interest for the development of new drug candidates with potential therapeutic activities including antibacterial, antifungal, antiviral, anticonvulsant, anticancer, antimalarial, antitubercular, anti-asthmatic, antidepressant, antidiabetic, antioxidant, antiparkinsonian, analgesic and antiinflammatory, etc. This review focuses on different synthetic approaches of oxadiazole derivatives under microwave heating method and study of their various biological activities.

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“…Traditional syntheses of α‐amino 1,3,4‐oxadiazoles are largely based on indirect condensation approaches where the oxadiazole unit is constructed through dehydration of a 1,2‐diacylhydrazine [2k, 4] . The need for multistep synthesis, and harsh dehydration conditions typically dictates that the oxadiazole be introduced at an early stage in the synthetic sequence, and thus a direct and late‐stage introduction of this motif would be both desirable and enabling [5]…”

Section: Figurementioning

confidence: 99%

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

Matheau‐Raven

¹

,

Dixon

²

2021

Angewandte Chemie

8

0

View full text Add to dashboard Cite

An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska's complex (IrCl(CO)(PPh 3) 2 ) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates. File list (2) download file view on ChemRxiv VaskaOxadiazoles -ChemRxiv.pdf (1.02 MiB) download file view on ChemRxiv VaskaOxadiazolesSI.pdf (4.98 MiB)

show abstract

A Review on the Preparation of 1,3,4-Oxadiazoles From the Dehydration of Hydrazines and Study of Their Biological Roles

Cited by 19 publications

References 54 publications

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

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